You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:51 UTC
Update Date2019-07-23 06:35:07 UTC
HMDB IDHMDB0041835
Secondary Accession Numbers
  • HMDB41835
Metabolite Identification
Common NameBenzidine
DescriptionBenzidine is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry. Benzidine, the trivial name for 4,4'-diaminobiphenyl, is the solid organic compound with the formula (C6H4NH2)2. This aromatic amine is a component of a test for cyanide and also in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer. Since August 2010 benzidine dyes are included in the EPA's List of Chemicals of Concern.
Structure
Data?1563863707
Synonyms
ValueSource
(1,1'-Biphenyl)-4,4'-diamineChEBI
4,4'-BianilineChEBI
4,4'-BiphenyldiamineChEBI
4,4'-BiphenylenediamineChEBI
4,4'-Diamino-1,1'-biphenylChEBI
4,4'-DiaminobiphenylChEBI
4,4'-DiaminodiphenylChEBI
4,4'-DiphenylenediamineChEBI
C.I. azoic diazo component 112ChEBI
p,P'-bianilineChEBI
p,P'-diaminodiphenylChEBI
p-DiaminodiphenylChEBI
4'-Amino[1,1'-biphenyl]-4-ylamine (acd/name 4.0)HMDB
4, 4'-BiphenylenediamineHMDB
Biphenyl -4,4'-ylenediamineHMDB
Fast corinth base bHMDB
p,P'-diaminobiphenylHMDB
p,P'-dianilineHMDB
p,p-BianilineHMDB
Rcra waste number u021HMDB
[1,1'-Biphenyl]-4,4'-diamineHMDB
[1,1'-Biphenyl]-4,4'-diamine (acd/name 4.0)HMDB
{[1,} 1'-biphenyl]-4,4'-diamineHMDB
Benzidine hydrochlorideHMDB
Benzidine acetateHMDB
Benzidine monosulfateHMDB
Benzidine dihydrochlorideHMDB
Chemical FormulaC12H12N2
Average Molecular Weight184.2371
Monoisotopic Molecular Weight184.100048394
IUPAC Name4-(4-aminophenyl)aniline
Traditional Namebenzidine
CAS Registry Number92-87-5
SMILES
NC1=CC=C(C=C1)C1=CC=C(N)C=C1
InChI Identifier
InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
InChI KeyHFACYLZERDEVSX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzidines. These are organic compounds containing the benzidine skeleton, made up of a biphenyl ring system substituted at the 4- and 4'-positions with a unsubstituted amine group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBenzidines
Alternative Parents
Substituents
  • Benzidine
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Role

Indirect biological role:

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point120 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.32 mg/mL at 25 °CNot Available
LogP1.34Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP1.59ALOGPS
logP1.96ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)4.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.6 m³·mol⁻¹ChemAxon
Polarizability21.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-1900000000-46465bd7171400dfc550Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-1900000000-46465bd7171400dfc550Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-da909bc8739471b977a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-0900000000-36d2368b345aadafe472Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-c5c1dcbf033fe4c60c26Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-d5e0ce902c65a7d945a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-527aa9bf80b633185478Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-d455d086a3a2f8252f64Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-0900000000-8a4d7fb696a251cf65f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-0900000000-9894faa005f0ae52dc53Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014r-0900000000-0b8ab8dbf459dd778773Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-497ea7121bf277833bb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-6af8bfce4a24520cec00Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-91749c0c5e4ef529093eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-49669661b9cd83218acbSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-a61957b37aba01bd4ee0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00kr-1900000000-c4a27064ec37d84f0355Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-5f242ea7ebce9e040adfSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-6ee5a8d18cf5b5e520e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-bfa10df85ed8a268fafcSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-fccc4a1798517c633d70Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-df132eef993f855e82edSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-000i-0900000000-888ac1ea798f6fefc1c9Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-000i-0900000000-0c52e47f06b81a2ba3abSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014r-0900000000-1ec70ed1fae32ff8da5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-3e38ba17e296f689d52cSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-ed1167d41dd159b83709Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-362a0103e0a9399a2407Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-0c34c7cea9097e35e7e1Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6844
KEGG Compound IDC16444
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzidine
METLIN IDNot Available
PubChem Compound7111
PDB IDNot Available
ChEBI ID80495
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Arlt M, Scheffler A, Suske I, Eschner M, Saragi TP, Salbeck J, Fuhrmann-Lieker T: Bipolar redox behaviour, field-effect mobility and transistor switching of the low-molecular azo glass AZOPD. Phys Chem Chem Phys. 2010 Nov 7;12(41):13828-34. doi: 10.1039/c0cp00643b. Epub 2010 Sep 20. [PubMed:20852800 ]
  2. Lardo MM, Diaz NB, Artaza JR, Carbia CD, Nazer R, Valdez R: [Vitamin E as protective agent against hemolysis in leprosy patients under dapsone treatment]. Medicina (B Aires). 1997;57(2):150-4. [PubMed:9532824 ]